By Devan Cole, CNN
(CNN) — When Judge Jeffrey Bryan took the bench Tuesday at his courtroom in downtown St. Paul, Minnesota, he had serious questions for the Trump administration: What happened to the personal property of some two dozen immigrant detainees, and why shouldn’t officials be held in contempt as a way of ensuring those items get returned?
The queries set off a lengthy and at times contentious hearing during which Bryan, an appointee of then-President Joe Biden, repeatedly sparred with the top federal prosecutor in Minnesota, in what has become the latest flashpoint in a fraught relationship between federal judges in the North Star State and administration officials.
The tension began during President Donald Trump’s immigration crackdown there earlier this year and continued as courts in recent weeks have identified repeated violations of their orders in cases brought by immigrants challenging their arrest and detention.
Many of those immigrants were ordered released after judges, including Bryan, concluded that they were being held unlawfully. But as they were processed in and out of detention facilities, noncitizens in some two dozen cases before Bryan lost cash, phones, clothing and critical documents such as passports, work permits and driver’s licenses.
Almost immediately after the hearing got underway, Bryan and Daniel Rosen, the US Attorney for the District of Minnesota, whom the judge summoned for the proceeding, found themselves locked in a war of words. Rosen, a Trump appointee, accused the judge of “smearing” him and one of his deputies by warning that they may be held accountable for contemptuous behavior.
But the stakes were quickly raised when Bryan, concerned by the possibility that Rosen would bow out of the hearing altogether, floated the possibility of imprisonment to compel his participation in the proceeding. That form of contempt is separate from the civil contempt the judge is weighing to ensure belongings are returned to the immigrants.
“I haven’t ruled out the consequence of imprisonment,” Bryan said. “Although I’ll be honest with you, sir, I think that that’s very, very unlikely.”
Making such a decision, the judge said, “would a historical low point for the office of the United States Attorney and for this District.”
The hearing ultimately continued and over the course of several hours, Rosen and attorneys for some of the immigrants informed Bryan that in recent days many of the possessions had been located and returned to the immigrants. Those resolutions had the effect of removing the threat of civil contempt, a prospective measure intended to force compliance with a court order.
The orders at issue were handed down when Bryan directed officials to release an immigrant detainee. The judge’s release order included a standard provision requiring officials with Immigration and Customs Enforcement to also return all property taken from the immigrant while they were held in custody.
As the hearing unfolded, it became clear that in three cases, unreturned property was working its way back to its owners, but that in two instances, the government had outright lost belongings. Those lost items include a woman’s driver’s license and a man’s car keys, cell phone and earphones.
“We take very seriously the fact that it’s lost. Property shouldn’t be lost, but property did get lost,” Rosen told Bryan as he argued that officials made good faith attempts to locate the property and that any further efforts to find the stuff would be “futile.”
“I think these fall into the realm of human error. Human error for which the petitioner is entitled to compensation,” he said, adding later: “There was no contempt of court. Not in one single order. There was no defiance, no disobedience, and that’s what’s required for contempt.”
Bryan did not make a decision from the bench and